Lactic Acid → Toremifene

HRID 2297331Notes

Reaction equation

HRID 2297331 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1)[CH3:3].[C:30]([OH:35])(=[O:34])[CH:31]([CH3:33])[OH:32]>CO>[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[CH2:15][CH2:16][Cl:17])=[CH:11][CH:12]=1)[CH3:3].[C:30]([O-:35])(=[O:34])[CH:31]([CH3:33])[OH:32].[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[CH2:15][CH2:16][Cl:17])=[CH:11][CH:12]=1)[CH3:3]

Participants

5

Reactant 2

HCID 612Lactic AcidHCID 3005573Toremifene

Product 2

HCID 3005573ToremifeneHCID 131723674HCID 131723674, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of toremifene base (1.00 g, 0.0025 moles) and methanol (20 ml) was slowly added lactic acid (223 μl, 0.0025 moles). The mixture was stirred for a while and evaporated to dryness. The lactate of toremifene was obtained as sticky white solid. 1H-NMR (d6-DMSO) d 7.38 (tt, 2H), 7.35-7.27 (m, 3H), 7.27-7.12 (m, 5H), 6.76 (d, 2H), 6.61 (d, 2H), 3.99 (q, 1H), 3.92 (t, 2H), 3.43 (t, 2H), 2.85 (t, 2H), 2.62 (t, 2H), 2.22 (s, 6H), 1.22 (d, 3H).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-702f90fa83cb4e58b13551909be3fed0
Source dataset
uspto-grants-2002_12
Patent number
US06491951B1

Reaction notes

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